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McCann started his career with Dundee before moving on to Heart of Midlothian in 1996. He helped the Tynecastle side win the Scottish Cup in 1998, their first major trophy in 36 years. McCann moved to Rangers later that year for £1.9 million.[3] He scored two goals against Rangers' arch-rivals Celtic on 2 May 1999 to clinch the SPL title. In 2003 Rangers' were forced to sell him due to their financial problems.[4]

He joined Southampton on 5 August 2003, for £1.5 million.[5] A series of injuries made it difficult for him to maintain his place in the team. McCann scored one goal for Southampton, in a League Cup tie against Northampton Town.[6] His contract with Southampton was terminated by mutual consent in January 2006.[7]

On 14 May 2008, it was announced that McCann had signed for SPL rivals Falkirk. He scored on his debut against former club Hearts,[10] and then scored twice for Falkirk in a League Cup tie against Queen of the South[11] and Inverness Caledonian Thistle.[12] He was released on 22 August 2009 after managerial changes at Falkirk, with outgoing manager John Hughes (the manager that signed him) being replaced by Eddie May.

On 12 February 2011, McCann came out of retirement to help Dundee stave-off relegation.[13] He scored a last minute goal in his first appearance, against Raith Rovers.

He made his debut for Scotland on 5 September 1998, as a late substitute for Ally McCoist in a 0–0 draw away to Lithuania. His first appearance in the starting line-up was on 31 March 1999 in a 2–1 home defeat to the Czech Republic. He scored three goals for Scotland, including two in consecutive matches in September 2003 during the qualifying rounds for Euro 2004. He continued to play regularly for Scotland until November 2005.[citation needed]